Triethylsilane → 1-Triethylsiloxy-spiro[4.5]decane-2-carboxylic acid methyl ester

HRID 2070554ノート

反応式

HRID 2070554 の反応式
[CH3:1][O:2][C:3](=[O:15])[CH:4]=[CH:5][CH2:6][C:7]1([CH:13]=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[CH2:16]([SiH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[CH3:17].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.[Rh]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]([CH:4]1[CH2:5][CH2:6][C:7]2([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:13]1[O:14][Si:18]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:16][CH3:17])=[O:15]

参加物

6

反応物 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 727655614-(1-Formyl-cyclohexyl)-but-2-enoic acid methyl ester

生成物 1

HCID 577713731-Triethylsiloxy-spiro[4.5]decane-2-carboxylic acid methyl ester

試薬・触媒・溶媒 2

HCID 178479813HCID 178479813、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
55 °C

実験手順

To a solution of 4-(1-formyl-cyclohexyl)-but-2-enoic acid methyl ester (3.7 g) obtained in Step 1 and tris(triphenylphosphine) rhodium(I) chloride (163 mg) in toluene (80 mL) was added dropwise triethylsilane (5.9 mL) under argon atmosphere over 10 minutes, followed by stirring the reaction mixture at 55° C. for 27 hours. After cooling down to room temperature and adding aqueous sodium bicarbonate solution, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=20:1) to give 1-triethylsiloxy-spiro[4.5]decane-2-carboxylic acid methyl ester (5.0 g).

後処理

  1. temperatureAfter cooling down to room temperature
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=20:1)

出典と根拠

ORDレコード
ord-6a4bf175861b44d8b777ae75cc01aa00
出典データセット
uspto-grants-2012_10
特許番号
US08299296B2

反応ノート

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